Selected filamentous fungi—98 strains of 31 genera—were screened for the ability to catalyze 11β-hydroxylation of 6α-fluoro-16α-methyl-deoxycorticosterone 21-acetate (FM-DCA). It was established that representatives of the genera Gongronella , Scopulariopsis , Epicoccum , and Curvularia have the ability to activate 11β-hydroxylase steroids. The strains of Curvularia lunata VKM F-644 and Gongronella butleri VKM F-1033 expressed maximal activity and formed 6α-fluoro-16α-methyl-corticosterone as a major bioconversion product from FM-DCA. The structures of the major products and intermediates of the bioconversion were confirmed by TLC, HPLC, MS and 1 H NMR analyses. Different pathways of 6α-fluoro-16α-methylcorticosterone formation by C. lunata and G. butleri strains were proposed based on intermediate identification. The constitutive character and membrane-binding localization were evidence of a 11β-hydroxylating system in G. butleri , while an inducible character and microsomal localization was confirmed for 11β-hydroxylase of C. lunata . Under optimized conditions, the molar yield of 6α-fluoro-16α-methyl-corticosterone reached 65% at a FM-DCA substrate loading of 6 g/L.